Although I can't speak to the Banner Elk market, I'd be happy to share any insight on just STR investing in general as it related to our experience in Western NC.Good luck!

Seller will be taking a 30k+ loss with this route.325k with 50K down to seller, 3 years of payments $1600/month, and a balloon payment of 215k at the end of 3 years.Benefits to me: (1) 10k less downpayment, (2) with the conventional route, the loan would be at 228k after 3 years of payments, so I will gain additional equity with the 2nd option since I will owe 215k (presumably I will have to refinance at that time).Benefit to seller: she gets over asking price, 50K upfront and $300/month of cash flow.Does this offer and structure sound reasonable?

When investing with them you get almost no tax benefits and usually get crappy management. 

Price point relative to what? 

This is a significant potential benefit that can impact everything from security deposits to rent controls to eviction procedures. 

You can get in while prices are still relatively low and watch as it grows quickly over the next few years. 

As someone relatively young, obtaining a conventional loan has proven challenging for me.

A HELOC should be reported on your credit profile as real-estate related.

Starting real estate investing early is a smart move, especially while leveraging your military benefits.

If the property was already listed on the MLS, I'd push back on the price relative to the comps.